Heterocyclic compounds

Abstract

A group of heterocyclic compounds useful in the treatment of disorders and diseases of the cardiovascular system and/or in the treatment of superficial and deep allergic phenomena is described. These compounds are piperidine compounds linked by the nitrogen atom to a substituted or unsubstituted phenyl radical through the intermediary of a group selected from a lower-alkylene radical, a mono-keto lower alkylene radical or a hydroxy-lower-alkylene radical, or a bivalent radical of the formula ##EQU1## or --O--(lower-alkylene)-. The piperidine rings are further substituted by a benzamido, substituted benzamido or cyclohexylcarboxamido residue.

We claim: 
     
       1. A compound selected from the group consisting of (A) heterocyclic compounds of the formula ##SPC10## in which W represents a member of the group consisting of phenyl, monohalophenyl, dihalophenyl, lower alkoxyphenyl, lower alkyl phenyl, di-(lower alkyl)phenyl, hydroxyphenyl, dihydroxyphenyl and acetylaminophenyl, A represents a bivalent radical selected from the group consisting of mono-keto lower alkylene, hydroxy lower alkylene, and radicals having the formula --OCH 2  CHOHCH 2  -- or O-lower alkylene; R represents a member of the group consisting of phenyl, chlorophenyl and cyclohexyl and the term "lower" means that the radical contains from 1 to 6 carbon atoms or W--A represents Ar 2  CHCH 2  (CH 2 ) n  --  where n denotes 1 to 4 and Ar represents phenyl or halophenyl; and (B) the pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.   
     
     
       2. A compound as claimed in claim 1, wherein A has the formula --CO.CH 2  CH 2  CH 2  --. 
     
     
       3. A compound as claimed in claim 1, which is 1-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]-4-benzamidopiperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       4. A compound as claimed in claim 1, which is 1-[4-fluorophenyl)-4-oxobutyl]-4-benzamidopiperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       5. A compound as claimed in claim 1, which is 4-benzamido-1-[4-(p-chlorophenyl)-4-oxobutyl]piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       6. A compound as claimed in claim 1, which is 1-[4-fluorophenyl)-4-hydroxybutyl]-4-benzamidopiperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       7. A compound as claimed in claim 1, which is 4-benzamido-1-(4-phenyl-4-oxo-butyl)piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       8. A compound as claimed in claim 1, which is 4-cyclohexanecarboxamido-1-(4-phenyl-4-oxobutyl)piperidine or a pharmaceutically acceptable non toxic salt thereof. 
     
     
       9. A compound as claimed in claim 1, which is (+)-4-benzamido-1-(4-phenyl-4-hydroxybutyl)piperidine. 
     
     
       10. A compound as claimed in claim 1, which is 1-(2-phenoxyethyl)-4-benzamidopiperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       11. A compound as claimed in claim 1, which is 4-benzamido-1-[4-(4-hydroxyphenyl)-4-oxobutyl]piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       12. A compound as claimed in claim 1, which is 4-(4-benzamidopiperid-1-yl)-1,1-di-p-fluorophenyl)butane or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       13. A compound as claimed in claim 1, which is 1-[1-(4-acetamidophenoxy)-2-hydroxy-prop-3-yl]-4-benzamidopiperidine. 
     
     
       14. A compound as claimed in claim 1, which is 1-(2-hydroxy-2-phenylethyl)-4-benzamidopiperidine. 
     
     
       15. A compound as claimed in claim 1, which is 4-benzamido-1-[4-(2,5-dimethylphenyl)-4-oxobutyl] piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       16. A compound as claimed in claim 1, which is 4-benzamido-1-[4-(2,4-dimethyl-phenyl)-4-oxobutyl] piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       17. A compound as claimed in claim 1, which is 4-benzamido-1-(3-phenyl-3-oxopropyl)piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       18. A compound as claimed in claim 1 which is 4-benzamido-1-[4-(4-methoxyphenyl)-4-oxobutyl] piperidine or a pharmaceutically acceptable acid addition salt thereof. 
     
     
       19. A compound as claimed in claim 1, which is 4-benzamido-1-[4-(4-tert-butyl-phenyl)-4-oxobutyl]piperidine or a pharmaceutically acceptable acid addition salt thereof.